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A1076

BAPTA-AM

Name: BAPTA-AM
Brand: SIGMA

≥95% (HPLC), powder, intracellular Ca²⁺ store chelator

Synonym(s):

1,2-Bis(2-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid tetrakis(acetoxymethyl ester)

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About This Item

Empirical Formula (Hill Notation):

C₃₄H₄₀N₂O₁₈

CAS Number:

126150-97-8

Molecular Weight:

764.68

NACRES:

NA.77

PubChem Substance ID:

24890502

UNSPSC Code:

12352200

MDL number:

MFCD00036696

Beilstein/REAXYS Number:

7458534

Assay:

≥95% (HPLC)

Form:

powder

Quality level:

200

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Properties

Product Name

BAPTA-AM, ≥95% (HPLC)

Quality Level

200

assay

≥95% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)c1ccccc1OCCOc2ccccc2N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O

InChI

1S/C34H40N2O18/c1-23(37)47-19-51-31(41)15-35(16-32(42)52-20-48-24(2)38)27-9-5-7-11-29(27)45-13-14-46-30-12-8-6-10-28(30)36(17-33(43)53-21-49-25(3)39)18-34(44)54-22-50-26(4)40/h5-12H,13-22H2,1-4H3

InChI key

YJIYWYAMZFVECX-UHFFFAOYSA-N

Description

General description

BAPTA-AM inhibits free radical-mediated toxicity, enhances apoptosis in non-neuronal cells and protects neurons from ischemic damage. It regulates ion channels and blocks neuronal Ca²⁺-activated K⁺ channel currents. BAPTA-AM maintains intracellular Ca²⁺ homeostasis.

Application

BAPTA-AM has been used :

to reduce the elevation of cleaved caspase-3
to block cell death, inhibit ROS (reactive oxygen species) production and inhibit caspase-8 activation
to exclude the effect of changes in intracellular Ca²⁺ ([Ca²⁺]_i) concentration during seizure induction
to eliminate the increase of [Ca²⁺]_i induced by 6-hydroxydopamine (6-OHDA)

Biochem/physiol Actions

Selective chelator of intracellular Ca²⁺ stores.

Other Notes

Membrane-permeable form of BAPTA.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Articles

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Detect, Visualize and Quantify Single Post-Translational Modifications

Sigma-Aldrich presents a Biofiles on Detect, Visualize and Quantify Single Post-Translational Modifications

BAPTA/AM, an intracellular calcium chelator, induces delayed necrosis by lipoxygenase-mediated free radicals in mouse cortical cultures

Wie MB, et al.

Progress in Neuro-Psychopharmacology & Biological Psychiatry, 25(8), 1641-1659 (2001)

The membrane permeable calcium chelator BAPTA-AM directly blocks human ether a-go-go-related gene potassium channels stably expressed in HEK 293 cells

Tang Q, et al.

Biochemical Pharmacology, 74(11), 1596-1607 (2007)

M-calpain activation facilitates seizure induced KCC2 down regulation

Wan L, et al.

Frontiers in Molecular Neuroscience, 11, 287-287 (2018)

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Global Trade Item Number

SKU	GTIN
A1076-25MG	04061833334867